5-chloro-2-(methylthio)benzaldehyde | 91827-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-2-(methylthio)benzaldehyde
• 英文别名: 5-chloro-2-methylsulfanylbenzaldehyde
• CAS: 91827-45-1
• 化学式: C₈H₇ClOS
• 分子量: 186.662
• InChiKey: SBTCGVVBXKUUPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(methylthio)benzaldehyde 在 sodium periodate 作用下， 以 乙醇 为溶剂， 反应 40.0h， 生成 5-<5'-chloro-2'-(methylsulfinyl)phenyl>imidazolidine-2,4-dione
  参考文献：
  名称：

  Rotationally restricted mimics of rigid molecules: nonspirocyclic hydantoin aldose reductase inhibitors

  摘要：

  Sorbinil (1), a spirocyclic hydantoin, is a potent inhibitor of the enzyme aldose reductase. Simulation of the rigid spirocyclic ring orientation found in sorbinil was achieved with nonspirocyclic 5-[5'-chloro-2'-(alkylsulfonyl)-phenyl]hydantoins and 5-[5'-chloro-2'-[(N-alkylamino)sulfonyl]phenyl]hydantoins. The 2'-substituent (SO2R) was sufficiently large to hinder rotation of the hydantoin ring, forcing an orientation similar to that of a spirocyclic hydantoin. Calculated conformational preference, X-ray data, and inhibitory IC50 values for these nonspirocyclic 2'-substituted (SO2R) phenylhydantoins are in accord with what is expected for spirocyclic hydantoins and comparable to those of sorbinil.

  DOI：

  10.1021/jm00126a011
• 作为产物：
  描述：

  4-chloro-2-(hydroxymethyl)thiophenol 在 manganese(IV) oxide 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 5-chloro-2-(methylthio)benzaldehyde
  参考文献：
  名称：

  Rotationally restricted mimics of rigid molecules: nonspirocyclic hydantoin aldose reductase inhibitors

  摘要：

  Sorbinil (1), a spirocyclic hydantoin, is a potent inhibitor of the enzyme aldose reductase. Simulation of the rigid spirocyclic ring orientation found in sorbinil was achieved with nonspirocyclic 5-[5'-chloro-2'-(alkylsulfonyl)-phenyl]hydantoins and 5-[5'-chloro-2'-[(N-alkylamino)sulfonyl]phenyl]hydantoins. The 2'-substituent (SO2R) was sufficiently large to hinder rotation of the hydantoin ring, forcing an orientation similar to that of a spirocyclic hydantoin. Calculated conformational preference, X-ray data, and inhibitory IC50 values for these nonspirocyclic 2'-substituted (SO2R) phenylhydantoins are in accord with what is expected for spirocyclic hydantoins and comparable to those of sorbinil.

  DOI：

  10.1021/jm00126a011

文献信息

• Chromium-catalyzed couplings of C(aryl)–SMe bonds for accessing arylated and alkylated benzaldehyde derivatives
  作者：Haohao Zeng、Shangru Yang、Chao Li、Fei Fan、Liang Ling、Meiming Luo、Xiaoming Zeng

  DOI：10.1039/d2cc01631a

  日期：——

  functionalized benzaldehydes under mild conditions. This reaction was promoted specifically by a low-cost and simple CrCl2 salt used as a precatalyst, enabling synchronous activations of ortho-C(aryl)–SMe and ortho′-C(aryl)–H bonds to achieve difunctionalization of benzaldimines. This work provided a strategy for accessing arylated, alkylated, and diarylated benzaldehyde derivatives as a result of

  这里描述的是铬催化的 C(芳基)-SMe 键断裂，导致在温和条件下与有机镁偶联得到官能化苯甲醛。该反应通过一种用作预催化剂的低成本且简单的 CrCl 2盐来特别促进，使邻-C(芳基)-SMe 和邻'-C(芳基)-H 键同步活化以实现苯扎亚胺的双官能化。由于 C(芳基)-SMe 和 C(芳基)-SMe/C(芳基)-H 键的偶联在具有成本效益的 Cr 催化作用下得到促进，这项工作提供了一种获取芳基化、烷基化和二芳基化苯甲醛衍生物的策略.
• From benzofuro-, benzothieno- and 10-methylindolo-[2,3-<i>b</i>]-fused benzothiopyrano[4,3,2-<i>de</i>]quinolines to the corresponding benzothiopyrano[4,3,2-<i>de</i>]1,8-naphthyridines: synthesis and properties of these hexacyclic heteroaromatic compounds
  作者：Nicolas Mast、William Erb、Lionel Nauton、Pascale Moreau、Olivier Mongin、Thierry Roisnel、Margaux Macaigne、Thomas Robert、Stéphane Bach、Laurent Picot、Valérie Thiéry、Jean-Pierre Hurvois、Florence Mongin

  DOI：10.1039/d2nj04567b

  日期：——

  and original syntheses are always required. Here, 1-aminothioxanthone was obtained either in four steps from commercially available thioxanthone, or in five steps from 3-fluoroaniline. As for 2-aminothioxanthone, direct N-arylation using commercial 2-chlorothioxanthone gave its Boc-protected derivative. From 1-aminothioxanthone, original 10-methylbenzothiopyrano[4,3,2-de]indolo[2,3-b]quinoline was synthesized

  多环杂环化合物如 1- 和 2- 氨基噻吨酮是具有不同性质的分子的重要前体，并且总是需要原始合成。在这里，1-氨基噻吨酮是从市售的噻吨酮分四步获得的，或者是从 3-氟苯胺分五步获得的。至于 2-氨基噻吨酮，使用商业 2-氯噻吨酮直接进行N-芳基化，得到其 Boc 保护的衍生物。以1-氨基噻吨酮为原料，利用2-碘-N通过串联N-芳基化-环化合成原始的10-甲基苯并噻喃[4,3,2- de ]吲哚[2,3 - b ]喹啉- 在铜存在下的甲基吲哚。然而，这种方法对 2-碘苯并噻吩的效率较低，我们还研究了另一种策略。接下来，我们的努力集中在苯并呋喃-、苯并噻吩并-和吲哚[2,3- b ]苯并噻喃并[4,3,2- de ]1,8-萘啶的合成上，它们是具有螺旋性质的原始六环。设计了不同的方法，我们通过五个步骤从 2-chloro-4-fluoropyridine 实现了我们的目标。将获得的原始多环化合
• Nematizide Mittel
  申请人：CIBA-GEIGY AG

  公开号：EP0454621A2

  公开（公告）日：1991-10-30

  Es werden nematizide Mittel, welche als Wirkstoff Verbindungen der Formel I worin    R Nitro oder Halogen bedeutet, ferner Verfahren zur Herstellung der Verbindungen der Formel I, neue Zwischenprodukte des Herstellungsverfahrens und Verfahren zur Verwendung der Wirkstoffe und der Mittel bei Bekämpfung von Nematoden beschrieben.

  含有式 I 化合物的杀线虫剂 其中 R 是硝基或卤素、式 I 化合物的制备工艺、制备工艺的新型中间体以及活性化合物和制剂用于防治线虫的工艺。
• Substituted benzylamino nitrogen containing non-aromatic heterocycles
  申请人：PFIZER INC.

  公开号：EP1114823A2

  公开（公告）日：2001-07-11

  The present invention relates to novel substituted benzylamino nitrogen containing nonaromatic heterocycles and, specifically, to compounds of formula (I) wherein W, R1, R2, R3 and A are as defined in the specification, and to intermediates used in the synthesis of such compounds. The novel compounds of formula (I) are useful in the treatment of inflammatory and central nervous system disorders, as well as other disorders.

  本发明涉及新型取代的含苄基氨基氮的非芳香族杂环，特别是涉及式（I）化合物（其中 W、R1、R2、R3 和 A 如说明书中所定义）以及用于合成此类化合物的中间体。式（I）的新型化合物可用于治疗炎症和中枢神经系统疾病以及其他疾病。
• Hodgson; Beard, Journal of the Chemical Society, 1927, p. 2427
  作者：Hodgson、Beard

  DOI：——

  日期：——